Record Information
Version1.0
StatusDetected and Quantified
Creation Date2020-12-10 18:50:51 UTC
Update Date2024-04-30 19:33:14 UTC
Metabolite IDMMDBc0000601
Metabolite Identification
Common NameL-Allothreonine
DescriptionL-allothreonine is the L-enantiomer of allothreonine. It has a role as an Escherichia coli metabolite and a Saccharomyces cerevisiae metabolite. It is an enantiomer of a D-allothreonine. It is a tautomer of a L-allothreonine zwitterion. Allothreonine is the substrate of the enzyme Serine hydroxymethyltransferase1 (SHMT, EC 2.1.2.1), a human cytoplasmic mRNA binding protein. SHMT uses pyridoxal 5'-phosphate (PLP) and tetrahydropteroylglutamate (H4PteGlu) as coenzymes and catalyzes the reversible interconversion of serine and glycine. In addition to these physiological reactions, SHMT also catalyzes, in the absence of H4PteGlu, the retroaldol cleavage of several 3-hydroxyamino acids, such as allothreonine. Allothreonine is a plant metabolite that appears in the human diet in variable concentrations depending on: plant species, physiological changes during plant growth, senescence, and reactions to environmental stress or to changes due to plant transformation (PMID:10858298 , 10952545 ).
Structure
Synonyms
ValueSource
(2S,3S)-2-Amino-3-hydroxybutanoic acidChEBI
Allo-L-threonineChEBI
ALLO-threonineChEBI
L-Allo-threonineChEBI
(2S,3S)-2-Amino-3-hydroxybutanoateGenerator
D-AllothreonineHMDB
Molecular FormulaC4H9NO3
Average Mass119.1192
Monoisotopic Mass119.058243159
IUPAC Name(2S,3S)-2-amino-3-hydroxybutanoic acid
Traditional NameL-allothreonine
CAS Registry NumberNot Available
SMILES
C[C@H](O)[C@H](N)C(O)=O
InChI Identifier
InChI=1S/C4H9NO3/c1-2(6)3(5)4(7)8/h2-3,6H,5H2,1H3,(H,7,8)/t2-,3-/m0/s1
InChI KeyAYFVYJQAPQTCCC-HRFVKAFMSA-N